title: O-methylasparvenone, a nitrogen-free serotonin antagonist.
abstract: O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT2C ligands and found to be 5-HT2C antagonists. They represent the first nitrogen-free serotonin ligands. The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester. A short and efficient synthesis of rac-1 was developed. This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established.
authors.affiliation: Pharma Division, Preclinical CNS Research, F. Hoffmann-La Roche Ltd, Basel, Switzerland.
authors.forename: M
authors.initials: M
authors.lastname: Bös
authors.forename: R
authors.initials: R
authors.lastname: Canesso
authors.forename: N
authors.initials: N
authors.lastname: Inoue-Ohga
authors.forename: A
authors.initials: A
authors.lastname: Nakano
authors.forename: Y
authors.initials: Y
authors.lastname: Takehana
authors.forename: A J
authors.initials: AJ
authors.lastname: Sleight
mesh_terms: D016475:3T3 Cells; D000818:Animals; D001230:Aspergillus; D051379:Mice; D008958:Models, Molecular; D009284:Naphthols / Q000302:isolation & purification* / Q000494:pharmacology; D011869:Radioligand Assay; D011985:Receptors, Serotonin / Q000378:metabolism; D012702:Serotonin Antagonists / Q000302:isolation & purification* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D009284:Naphthols; C111197:O-methylasparvenone; D011985:Receptors, Serotonin; D012702:Serotonin Antagonists; C010292:asparvenone